How I spent a year “strategically broke” (pics and number inside)

🌈 Abstract

The article discusses the author's experience of spending a year "Strategically Broke" - with no job, no salary, and no plan - after college, and how that decision ultimately helped him find his career path. It covers the author's backstory, the strategies he used to live frugally and fund his year of exploration, and the key skills he developed during that time. The article also introduces the author's "Permission to Wander" 3-step system for figuring out one's career path.

🙋 Q&A

[01] How the Author Spent a Year "Strategically Broke"

1. What was the author's motivation for spending a year "Strategically Broke" after college?

• The author was inspired by a quote he heard from someone at a casino: "I don't know much, but I know one thing: the ordinary life isn't for me." This made him want to live a life where he could be creative, spend time with friends, and get financially successful.

2. How did the author fund his year of exploration?

• The author and his two friends rented a cheap apartment in Boulder, Colorado and lived very frugally, eating inexpensive meals and using secondhand furniture.
• The author found part-time tutoring gigs that provided $700 per month for 5 hours of work per week.
• He also entered and won several business plan competitions, earning over $25,000 in prize money to cover living expenses for nearly 2 years.

3. What did the author do with his free time during that year?

• The author used his free time to travel extensively, road tripping across the United States and then going to international destinations like China, Bali, and Australia.
• He also worked on developing various skills, including video editing, cold emailing, and e-commerce, through a process of launching projects, getting feedback, and iterating to improve.

[02] The "Permission to Wander" System

1. What is the "Permission to Wander" system the author used to figure out his career path? The author will explain the "Permission to Wander" 3-step system in Part II of the essay, which is coming the next day. The summary does not cover the details of this system, as they are not provided in the current document.